Additive-controlled stereoselective glycosylations of 2,3-oxazolidinone protected glucosamine or galactosamine thioglycoside donors with phenols based on preactivation protocol

Abstract

Stereo-controllable glycosylation reactions of 2,3-oxazolidinone protected glucosamine thioglycoside donor with different phenol acceptors based on preactivation protocol, are described. It was found that BF3·Et2O worked as α-directing additive, while TTBP acted as β-directing additive. Simply by altering additives, either α-aryl glycosides or β-aryl glycosides were achieved in a stereoselective manner. The additives were also applied to the stereoselective glycosylation reactions of 2,3-oxazolidinone protected galactosamine donor with phenol substrates.

Keywords: Additive; Aryl glycoside; Glycosylation; Preactivation; Stereoselectivity.